Calvin began performing in Gainesville, Florida during his sophomore year at the University of Florida. He co-founded the University Stand-Up Comedy Club there, acting as its president for two consecutive years.
Now based in New York, Calvin was the MVP of the 2010 National Champion UF comedy team as voted at the Aspen Rooftop Comedy Festival. He was also named the Funniest College Student in America at the TBS Just for Laughs Festival in Chicago.